This chapter explores the multifaceted role and range of responsibilities of a chief executive officer (CEO). The CEO is often seen as the chief strategist in most companies. In football, the CEO is the clear strategic leader and someone who is charged with establishing a disciplined approach to what ‘fits’ the overall club strategy. In this view, the CEO ‘owns’ the strategy and is ultimately accountable for its success or failure. The focus of the first part of this chapter is on establishing the theoretical roles and responsibilities of the CEO within a business. The second half of the chapter uses a case study interview with a high-ranking EPL CEO to discuss club strategy and the process of ‘hiring and firing’ key personnel. Within this discussion, trust and risk are highlighted as major components of the executive decision-making process.